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Significant Enhancement in the Efficiency and Selectivity of Iron‐Catalyzed Oxidative Cross‐Coupling of Phenols by Fluoroalcohols
Author(s) -
Gaster Eden,
Vainer Yulia,
Regev Almog,
Narute Sachin,
Sudheendran Kavitha,
Werbeloff Aviya,
Shalit Hadas,
Pappo Doron
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409694
Subject(s) - chemoselectivity , phenols , catalysis , phenol , chemistry , selectivity , oxidative coupling of methane , oxidative phosphorylation , organic chemistry , combinatorial chemistry , biochemistry
Significant enhancement of both the rate and the chemoselectivity of iron‐catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), and 1‐phenyl‐2,2,2‐trifluoroethanol. The generality of this effect was examined for the cross‐coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs) and of phenol with β‐dicarbonyl compounds. The new conditions were utilized in the synthesis of 2′′′‐dehydroxycalodenin B in only four synthetic steps.